data_gjy20181101
_audit_creation_date               2018-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number             2014-1
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety           'C24 H14 F6 N2 O3'
_chemical_formula_sum              'C24 H14 F6 N2 O3'
_chemical_formula_weight           492.37
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             61
_space_group_name_H-M_alt          'P b c a'
_space_group_name_Hall             '-P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'

_cell_length_a                     18.6397(7)
_cell_length_b                     11.6276(6)
_cell_length_c                     20.5913(9)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       4462.9(3)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      6864
_cell_measurement_temperature      293(2)
_cell_measurement_theta_max        24.9750
_cell_measurement_theta_min        3.7980
_shelx_estimated_absorpt_T_max     0.992
_shelx_estimated_absorpt_T_min     0.987
_exptl_absorpt_coefficient_mu      0.131
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.61117
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.466
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               2000
_exptl_crystal_size_max            0.1
_exptl_crystal_size_mid            0.09
_exptl_crystal_size_min            0.06
_exptl_special_details
;
 ?
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0252
_diffrn_reflns_av_unetI/netI       0.0241
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.904
_diffrn_reflns_limit_h_max         23
_diffrn_reflns_limit_h_min         -25
_diffrn_reflns_limit_k_max         15
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         26
_diffrn_reflns_limit_l_min         -26
_diffrn_reflns_number              25753
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.904
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           29.283
_diffrn_reflns_theta_min           3.430
_diffrn_ambient_temperature        293(2)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   8.0353
_diffrn_detector_type              EosS2
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.904
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -83.00   1.00   1.00   20.40    --  -15.76 -57.00 -60.00   84
  2  ω    -85.00  54.00   1.00   20.40    --  -15.76   0.00   0.00  139
  3  ω    -32.00  15.00   1.00   20.40    --  -15.76  57.00  90.00   47
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type   
 'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.0168808000
_diffrn_orient_matrix_UB_12        0.0251126000
_diffrn_orient_matrix_UB_13        0.0274393000
_diffrn_orient_matrix_UB_21        -0.0116723000
_diffrn_orient_matrix_UB_22        -0.0466337000
_diffrn_orient_matrix_UB_23        0.0194814000
_diffrn_orient_matrix_UB_31        0.0320734000
_diffrn_orient_matrix_UB_32        -0.0301998000
_diffrn_orient_matrix_UB_33        -0.0073344000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3476
_reflns_number_total               5511
_reflns_odcompleteness_completeness  99.65
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       26.32
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_collection         'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction          'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           1.143
_refine_diff_density_min           -0.439
_refine_diff_density_rms           0.081
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.466
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       316
_refine_ls_number_reflns           5511
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.1469
_refine_ls_R_factor_gt             0.1083
_refine_ls_restrained_S_all        1.466
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.3634
_refine_ls_wR_factor_ref           0.3985
_refine_special_details
;
 ?
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C17(H17), C23(H23), C20(H20), C13(H13), C15(H15), C16(H16),
 C22(H22), C14(H14), C10(H10), C6(H6), C8(H8), C9(H9), C7(H7)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 N1 N 0.63098(13) 0.7514(2) 0.67636(13) 0.0448(7) Uani 1 1 d . . . . .
 O1 O 0.46422(19) 0.6654(3) 0.89507(14) 0.0996(12) Uani 1 1 d . . . . .
 F1 F 0.63367(19) 0.7004(3) 0.47722(14) 0.1166(12) Uani 1 1 d . . . . .
 N2 N 0.77975(17) 0.8992(3) 0.60554(18) 0.0725(10) Uani 1 1 d . . . . .
 C18 C 0.58616(15) 0.7237(3) 0.73104(15) 0.0454(7) Uani 1 1 d . . . . .
 C12 C 0.54698(16) 0.6755(3) 0.59266(15) 0.0474(8) Uani 1 1 d . . . . .
 C11 C 0.61323(15) 0.7354(3) 0.61152(16) 0.0463(8) Uani 1 1 d . . . . .
 C4 C 0.69489(15) 0.8093(3) 0.68307(16) 0.0489(8) Uani 1 1 d . . . . .
 F2 F 0.6616(3) 0.8725(3) 0.47405(15) 0.1309(13) Uani 1 1 d . . . . .
 F3 F 0.74156(18) 0.7526(4) 0.48670(17) 0.1393(16) Uani 1 1 d . . . . .
 F5 F 0.3860(2) 0.5747(3) 0.95231(16) 0.1568(19) Uani 1 1 d . . . . .
 C2 C 0.66835(17) 0.7830(3) 0.57595(16) 0.0496(8) Uani 1 1 d . . . . .
 C5 C 0.72652(17) 0.8398(3) 0.74668(16) 0.0534(8) Uani 1 1 d . . . . .
 C3 C 0.71800(15) 0.8299(3) 0.62016(16) 0.0504(8) Uani 1 1 d . . . . .
 C19 C 0.52248(18) 0.7830(3) 0.73982(19) 0.0584(9) Uani 1 1 d . . . . .
 H19 H 0.5079 0.8369 0.7092 0.070 Uiso 1 1 calc R . . . .
 C21 C 0.5046(2) 0.6799(3) 0.83784(17) 0.0642(11) Uani 1 1 d . . . . .
 O3 O 0.7799(2) 0.9542(5) 0.55567(18) 0.1294(17) Uani 1 1 d . . . . .
 C17 C 0.53172(18) 0.5658(3) 0.61303(19) 0.0602(9) Uani 1 1 d . . . . .
 H17 H 0.5646 0.5269 0.6390 0.072 Uiso 1 1 calc R . . . .
 C1 C 0.6763(2) 0.7767(4) 0.50452(18) 0.0630(10) Uani 1 1 d . . . . .
 C23 C 0.60733(19) 0.6414(4) 0.77427(18) 0.0621(10) Uani 1 1 d . . . . .
 H23 H 0.6492 0.5999 0.7667 0.075 Uiso 1 1 calc R . . . .
 C20 C 0.4803(2) 0.7623(3) 0.7941(2) 0.0663(11) Uani 1 1 d . . . . .
 H20 H 0.4376 0.8018 0.8010 0.080 Uiso 1 1 calc R . . . .
 C13 C 0.4964(2) 0.7314(3) 0.5535(2) 0.0636(10) Uani 1 1 d . . . . .
 H13 H 0.5046 0.8066 0.5401 0.076 Uiso 1 1 calc R . . . .
 C15 C 0.4210(2) 0.5664(4) 0.55467(19) 0.0685(11) Uani 1 1 d . . . . .
 H15 H 0.3798 0.5287 0.5407 0.082 Uiso 1 1 calc R . . . .
 C16 C 0.4686(2) 0.5123(4) 0.5957(2) 0.0704(11) Uani 1 1 d . . . . .
 H16 H 0.4581 0.4394 0.6118 0.085 Uiso 1 1 calc R . . . .
 C22 C 0.5669(2) 0.6193(4) 0.82936(18) 0.0749(12) Uani 1 1 d . . . . .
 H22 H 0.5816 0.5649 0.8597 0.090 Uiso 1 1 calc R . . . .
 C14 C 0.4350(2) 0.6757(4) 0.5348(2) 0.0749(12) Uani 1 1 d . . . . .
 H14 H 0.4023 0.7133 0.5081 0.090 Uiso 1 1 calc R . . . .
 F6 F 0.4331(3) 0.4894(3) 0.8738(3) 0.199(3) Uani 1 1 d . . . . .
 C10 C 0.7013(2) 0.9301(4) 0.7821(2) 0.0747(12) Uani 1 1 d . . . . .
 H10 H 0.6633 0.9737 0.7663 0.090 Uiso 1 1 calc R . . . .
 C24 C 0.4176(3) 0.5845(4) 0.8984(2) 0.0868(16) Uani 1 1 d . . . . .
 O2 O 0.8220(2) 0.9187(6) 0.6494(2) 0.177(3) Uani 1 1 d . . . . .
 C6 C 0.7826(2) 0.7781(4) 0.7710(2) 0.0794(13) Uani 1 1 d . . . . .
 H6 H 0.8011 0.7168 0.7472 0.095 Uiso 1 1 calc R . . . .
 C8 C 0.7880(3) 0.8960(5) 0.8637(2) 0.0935(17) Uani 1 1 d . . . . .
 H8 H 0.8095 0.9177 0.9025 0.112 Uiso 1 1 calc R . . . .
 C9 C 0.7312(3) 0.9569(5) 0.8403(2) 0.0897(15) Uani 1 1 d . . . . .
 H9 H 0.7127 1.0176 0.8644 0.108 Uiso 1 1 calc R . . . .
 C7 C 0.8128(3) 0.8056(6) 0.8311(3) 0.1043(19) Uani 1 1 d . . . . .
 H7 H 0.8498 0.7613 0.8482 0.125 Uiso 1 1 calc R . . . .
 F4 F 0.3649(3) 0.6039(7) 0.8557(3) 0.214(3) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 N1 C18 1.439(4) . ?
 N1 C11 1.388(4) . ?
 N1 C4 1.375(4) . ?
 O1 C21 1.409(4) . ?
 O1 C24 1.282(5) . ?
 F1 C1 1.316(5) . ?
 N2 C3 1.437(4) . ?
 N2 O3 1.209(5) . ?
 N2 O2 1.219(5) . ?
 C18 C19 1.384(4) . ?
 C18 C23 1.365(5) . ?
 C12 C11 1.470(4) . ?
 C12 C17 1.373(5) . ?
 C12 C13 1.400(5) . ?
 C11 C2 1.378(4) . ?
 C4 C5 1.479(5) . ?
 C4 C3 1.386(4) . ?
 F2 C1 1.307(5) . ?
 F3 C1 1.302(5) . ?
 F5 C24 1.262(4) . ?
 C2 C3 1.408(5) . ?
 C2 C1 1.480(5) . ?
 C5 C10 1.362(6) . ?
 C5 C6 1.364(5) . ?
 C19 C20 1.387(5) . ?
 C21 C20 1.391(6) . ?
 C21 C22 1.369(6) . ?
 C17 C16 1.378(5) . ?
 C23 C22 1.386(5) . ?
 C13 C14 1.371(5) . ?
 C15 C16 1.378(6) . ?
 C15 C14 1.360(6) . ?
 F6 C24 1.250(6) . ?
 C10 C9 1.357(6) . ?
 C24 F4 1.337(8) . ?
 C6 C7 1.397(7) . ?
 C8 C9 1.361(8) . ?
 C8 C7 1.329(8) . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C11 N1 C18 125.7(2) . . ?
 C4 N1 C18 122.3(3) . . ?
 C4 N1 C11 111.7(3) . . ?
 C24 O1 C21 119.7(3) . . ?
 O3 N2 C3 118.4(4) . . ?
 O3 N2 O2 122.0(4) . . ?
 O2 N2 C3 117.8(3) . . ?
 C19 C18 N1 119.3(3) . . ?
 C23 C18 N1 120.0(3) . . ?
 C23 C18 C19 120.8(3) . . ?
 C17 C12 C11 122.2(3) . . ?
 C17 C12 C13 117.9(3) . . ?
 C13 C12 C11 119.9(3) . . ?
 N1 C11 C12 121.2(3) . . ?
 C2 C11 N1 106.2(3) . . ?
 C2 C11 C12 132.6(3) . . ?
 N1 C4 C5 123.5(3) . . ?
 N1 C4 C3 105.0(3) . . ?
 C3 C4 C5 131.5(3) . . ?
 C11 C2 C3 107.6(3) . . ?
 C11 C2 C1 125.6(3) . . ?
 C3 C2 C1 126.6(3) . . ?
 C10 C5 C4 121.4(3) . . ?
 C10 C5 C6 118.2(4) . . ?
 C6 C5 C4 120.3(4) . . ?
 C4 C3 N2 122.8(3) . . ?
 C4 C3 C2 109.5(3) . . ?
 C2 C3 N2 127.4(3) . . ?
 C18 C19 C20 120.3(3) . . ?
 C20 C21 O1 116.7(4) . . ?
 C22 C21 O1 119.9(4) . . ?
 C22 C21 C20 123.2(3) . . ?
 C12 C17 C16 121.2(3) . . ?
 F1 C1 C2 113.5(3) . . ?
 F2 C1 F1 104.1(4) . . ?
 F2 C1 C2 114.4(3) . . ?
 F3 C1 F1 107.4(3) . . ?
 F3 C1 F2 104.1(4) . . ?
 F3 C1 C2 112.6(4) . . ?
 C18 C23 C22 120.4(4) . . ?
 C19 C20 C21 117.2(3) . . ?
 C14 C13 C12 120.3(4) . . ?
 C14 C15 C16 119.2(3) . . ?
 C15 C16 C17 120.1(4) . . ?
 C21 C22 C23 118.0(4) . . ?
 C15 C14 C13 121.1(4) . . ?
 C9 C10 C5 120.6(5) . . ?
 O1 C24 F4 109.8(5) . . ?
 F5 C24 O1 115.4(4) . . ?
 F5 C24 F4 104.5(5) . . ?
 F6 C24 O1 118.1(5) . . ?
 F6 C24 F5 112.6(5) . . ?
 F6 C24 F4 93.0(5) . . ?
 C5 C6 C7 120.9(5) . . ?
 C7 C8 C9 120.2(5) . . ?
 C10 C9 C8 120.8(5) . . ?
 C8 C7 C6 119.2(5) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.671
_oxdiff_exptl_absorpt_empirical_full_min  0.672
